The ultimate objective of this proposed research program is to devise successful and rational synthetic schemes for building two important antifungal antibiotics: 1-trichodermol (1) and 1-LL-Z1271 alpha (2). The strategy of each scheme is such that one should be able to perform the synthesis in the laboratory with simplicity and brevity. Each plan involves new synthetic method or design in order to broaden the scope of organic chemistry. The synthesis of antifungal antibiotics is particularly relevant because of the fundamental importance of these compounds in the treatment of disease. The proposed synthetic plans can be easily altered at various stages to allow introduction of structural modifications which may enhance the desired biological properties of these antibiotics. A national survey showed that serious, potentially fatal fungal diseases are on the increase and that these diseases are exceedingly difficult to diagnose and treat. We feel that the proposed research program will make both important and significant contributions to modern organic chemistry.